The reality is that if you are drawing objects to scale houses are very small. streets are very narrow and trees are really high, so much so that when drawing fantasy maps one usually throws scale out of the window and increases the size of houses and streets to get a more 'artistic' outcome. Not sure if this helps, but if you are after what scale is like, just use google earth and use the scale there as a guide.

welcome to the Guild, by the way!